Ethyl 4-[(4-nitrobenzyl)amino]-4-oxobutanoate → Ethyl 4-((4-aminobenzyl)amino)-4-oxobutanoate

HRID 30690Notes

Reaction equation

HRID 30690 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][NH:9][C:10](=[O:18])[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:6][CH:5]=1)([O-])=O>[C].[Pd].C(O)C>[NH2:1][C:4]1[CH:20]=[CH:19][C:7]([CH2:8][NH:9][C:10](=[O:18])[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 47312066Ethyl 4-[(4-nitrobenzyl)amino]-4-oxobutanoate

Product 1

HCID 69208897Ethyl 4-((4-aminobenzyl)amino)-4-oxobutanoateYield 40.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 4-[(4-nitrobenzyl)amino]-4-oxobutanoate (10 g), 10% palladium carbon (1 g) and ethanol (300 ml) was stirred under a hydrogen atmosphere at room temperature for 14 hrs. Palladium carbon was removed from the reaction mixture by filtration, and the filtrate was concentrated. Recrystallization of the residue from ethyl acetate-hexane gave ethyl 4-[(4-aminobenzyl)amino]-4-oxobutanoate (3.6 g, 40%) as colorless prism crystals. melting point: 62-64° C.

Workup

  1. customPalladium carbon was removed from the reaction mixture by filtration
  2. concentrationthe filtrate was concentrated
  3. customRecrystallization of the residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-82ab0a1500664be8a3352026487ef272
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

Loading…